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185 places from Chicago with a recent return price. Prices we can stand behind come first, then the cheapest.
From $228 round trip
20.3% below the middle price here: the cheapest return fare on each of 33 departure dates is usually $252 to $306.
This trip has 1 stop.
The map isn't ready yet. Everything is in the list.
| City | From | Dates | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| Fort Lauderdale FLL | $166 | 16 Nov – 20 Nov · 4 nights | MDW → FLL | out 1 stop, back 1 stop | found 19 hours ago | See prices for these dates |
| San Juan SJU | $196 | 5 Dec – 12 Dec · 7 nights | MDW → SJU | out 1 stop, back 1 stop | found today | See prices for these dates |
| New York NYC | $228 | 26 Nov – 1 Dec · 5 nights | MDW → EWR | out 1 stop, back 1 stop | found 16 hours ago | See prices for these dates |
| Orlando ORL | $236 | 16 Nov – 25 Nov · 9 nights | MDW → MCO | out 1 stop, back 1 stop | found 19 hours ago | See prices for these dates |
| Los Angeles LAX | $253 | 30 Nov – 15 Dec · 15 nights | MDW → LAX | out 1 stop, back 1 stop | found 6 hours ago | See prices for these dates |
| Detroit DTT | $274 | 8 Dec – 9 Dec · 1 night | MDW → DTW | out 1 stop, back 1 stop | found yesterday |
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work
| See prices for these dates |
| Denver DEN | $298 | 20 Nov – 20 Nov | MDW → DEN | out nonstop, back 1 stop | found today | See prices for these dates |
| Houston HOU | $305 | 25 Nov – 27 Nov · 2 nights | MDW → IAH | out 1 stop, back nonstop | found today | See prices for these dates |
| Tampa TPA | $310 | 27 Oct – 29 Oct · 2 nights | MDW → TPA | out 1 stop, back 1 stop | found today | See prices for these dates |
| Phoenix PHX | $334 | 11 Nov – 20 Nov · 9 nights | MDW → PHX | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| Baltimore BWI | $364 | 20 Oct – 22 Oct · 2 nights | MDW → BWI | out 1 stop, back 1 stop | found today | See prices for these dates |
| Pittsburgh PIT | $376 | 2 Jan 2027 – 6 Jan 2027 · 4 nights | MDW → PIT | out nonstop, back nonstop | found today | See prices for these dates |
| San Francisco SFO | $405 | 14 Apr 2027 – 17 Apr 2027 · 3 nights | MDW → SFO | out nonstop, back nonstop | found today | See prices for these dates |
| Tucson TUS | $473 | 10 Jan 2027 – 15 Jan 2027 · 5 nights | MDW → TUS | out nonstop, back nonstop | found yesterday | See prices for these dates |
| Omaha OMA | $476 | 9 Dec – 3 Jan 2027 · 25 nights | MDW → OMA | out nonstop, back nonstop | found yesterday | See prices for these dates |
| Sarasota SRQ | $476 | 27 Oct – 29 Oct · 2 nights | MDW → SRQ | out 2 stops, back 1 stop | found today | See prices for these dates |
| Ottawa YOW | $612 | 14 Nov – 17 Nov · 3 nights | MDW → YOW | out 1 stop, back 3 stops | found today | See prices for these dates |
| Punta Cana PUJ | $623 | 13 Dec – 20 Dec · 7 nights | MDW → PUJ | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| Salt Lake City SLC | $650 | 25 Oct – 28 Oct · 3 nights | MDW → SLC | out nonstop, back nonstop | found yesterday | See prices for these dates |
| Guatemala City GUA | $699 | 16 Nov – 1 Dec · 15 nights | MDW → GUA | out 2 stops, back 1 stop | found today | See prices for these dates |
| Mexico City MEX | $712 | 20 Oct – 31 Oct · 11 nights | MDW → MEX | out 1 stop, back 1 stop | found today | See prices for these dates |
| Cancun CUN | $794 | 13 Jan 2027 – 24 Jan 2027 · 11 nights | MDW → CUN | out 1 stop, back 1 stop | found today | See prices for these dates |
| Morelia MLM | $868 | 3 Jan 2027 – 4 Jan 2027 · 1 night | MDW → MLM | out nonstop, back 3 stops | found yesterday | See prices for these dates |
| Toronto YTO | $1,054 | 28 Oct – 8 Nov · 11 nights | MDW → YYZ | out 1 stop, back 1 stop | found today | See prices for these dates |
| Munich MUC | $1,192 | 6 Apr 2027 – 23 Apr 2027 · 17 nights | MDW → MUC | out 2 stops, back 2 stops | found today | See prices for these dates |
| Kailua-Kona KOA | $1,220 | 12 Feb 2027 – 19 Feb 2027 · 7 nights | MDW → KOA | out 1 stop, back 2 stops | found yesterday | See prices for these dates |
| City of Angeles CRK | $1,493 | 13 Nov – 4 Dec · 21 nights | MDW → CRK | out 3 stops, back 3 stops | found yesterday | See prices for these dates |
| Shanghai SHA | $1,509 | 31 Oct – 14 Nov · 14 nights | MDW → PVG | out 2 stops, back 3 stops | found yesterday | See prices for these dates |
| Santiago SCL | $1,569 | 24 Nov – 2 Dec · 8 nights | MDW → SCL | out 2 stops, back 3 stops | found today | See prices for these dates |
| Tashkent TAS | $1,632 | 26 Nov – 30 Dec · 34 nights | MDW → TAS | out 2 stops, back 2 stops | found 9 hours ago | See prices for these dates |
| Bishkek BSZ | $1,920 | 3 Apr 2027 – 8 May 2027 · 35 nights | MDW → BSZ | out 2 stops, back 2 stops | found yesterday | See prices for these dates |
| Kigali KGL | $2,205 | 24 Dec – 14 Jan 2027 · 21 nights | MDW → KGL | out 3 stops, back 3 stops | found today | See prices for these dates |
| Kinshasa FIH | $2,257 | 1 Dec – 22 Dec · 21 nights | MDW → FIH | out 3 stops, back 3 stops | found yesterday | See prices for these dates |
| Tbilisi TBS | $2,873 | 21 Dec – 12 Jan 2027 · 22 nights | MDW → TBS | out 2 stops, back 2 stops | found yesterday | See prices for these dates |
| Jeddah JED | $2,999 | 3 Jan 2027 – 17 Jan 2027 · 14 nights | MDW → JED | out 2 stops, back 2 stops | found yesterday | See prices for these dates |
| Saint Martin SFG | $3,248 | 19 Dec – 3 Jan 2027 · 15 nights | MDW → SFG | out 4 stops, back 3 stops | found today | See prices for these dates |
| Dallas DFW | $223 | 30 Dec – 2 Jan 2027 · 3 nights | MDW → DFW | out nonstop, back nonstop | found 3 days ago | See prices for these dates |
| Philadelphia PHL | $277 | 15 Jan 2027 – 18 Jan 2027 · 3 nights | MDW → PHL | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| Jacksonville JAX | $393 | 22 Oct – 23 Oct · 1 night | MDW → JAX | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| Reynosa REX | $552 | 5 Mar 2027 – 7 Mar 2027 · 2 nights | MDW → REX | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Puerto Vallarta PVR | $614 | 26 Oct – 28 Oct · 2 nights | MDW → PVR | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| Norfolk ORF | $643 | 26 Dec – 30 Dec · 4 nights | MDW → ORF | out 2 stops, back 2 stops | found 3 days ago | See prices for these dates |
| Puebla PBC | $670 | 20 Oct – 13 Nov · 24 nights | MDW → PBC | out 2 stops, back 1 stop | found 2 days ago | See prices for these dates |
| Freeport FPO | $718 | 19 Dec – 24 Dec · 5 nights | MDW → FPO | out 2 stops, back 2 stops | found 3 days ago | See prices for these dates |
| San Jose Del Cabo SJD | $769 | 13 Feb 2027 – 13 Mar 2027 · 28 nights | MDW → SJD | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| Bangkok BKK | $1,224 | 10 Feb 2027 – 24 Feb 2027 · 14 nights | MDW → BKK | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Manchester MAN | $1,333 | 4 Dec – 14 Dec · 10 nights | MDW → MAN | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Glasgow GLA | $1,371 | 25 Dec – 6 Jan 2027 · 12 nights | MDW → GLA | out 2 stops, back 2 stops | found 3 days ago | See prices for these dates |
| Abu Dhabi AUH | $1,581 | 11 Nov – 20 Nov · 9 nights | MDW → AUH | out 2 stops, back 2 stops | found 3 days ago | See prices for these dates |
| Barcelona BCN | $1,619 | 17 Dec – 11 Jan 2027 · 25 nights | MDW → BCN | out 1 stop, back 2 stops | found 3 days ago | See prices for these dates |
| Cairo CAI | $1,763 | 1 Jan 2027 – 17 Jan 2027 · 16 nights | MDW → CAI | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| Johannesburg JNB | $2,006 | 15 Mar 2027 – 30 Mar 2027 · 15 nights | MDW → JNB | out 2 stops, back 2 stops | found 3 days ago | See prices for these dates |
| Ulaanbaatar UBN | $2,740 | 16 Dec – 25 Dec · 9 nights | MDW → UBN | out 2 stops, back 3 stops | found 2 days ago | See prices for these dates |
| Mahe SEZ | $4,011 | 20 Feb 2027 – 12 Mar 2027 · 20 nights | MDW → SEZ | out 2 stops, back 2 stops | found 3 days ago | See prices for these dates |
| Atlanta ATL | $150 | 1 Dec – 17 Dec · 16 nights | MDW → ATL | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
| Miami MIA | $193 | 16 Nov – 21 Nov · 5 nights | MDW → MIA | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Las Vegas LAS | $201 | 5 Dec – 8 Dec · 3 nights | MDW → LAS | out 1 stop, back nonstop | found 4 days ago | See prices for these dates |
| Ontario ONT | $241 | 30 Oct – 2 Nov · 3 nights | MDW → ONT | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Raleigh RDU | $254 | 29 Dec – 4 Jan 2027 · 6 nights | MDW → RDU | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| New Orleans MSY | $255 | 18 Nov – 22 Nov · 4 nights | MDW → MSY | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Washington WAS | $276 | 14 Jan 2027 – 19 Jan 2027 · 5 nights | MDW → DCA | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
| Boston BOS | $308 | 30 Oct – 1 Nov · 2 nights | MDW → BOS | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Columbus CMH | $350 | 14 Jan 2027 – 28 Feb 2027 · 45 nights | MDW → CMH | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
| Guadalajara GDL | $351 | 6 Nov – 23 Nov · 17 nights | MDW → GDL | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
| Buffalo BUF | $378 | 26 Nov – 29 Nov · 3 nights | MDW → BUF | out nonstop, back 1 stop | found 5 days ago | See prices for these dates |
| Montego Bay MBJ | $380 | 9 Nov – 14 Nov · 5 nights | MDW → MBJ | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| Fort Myers FMY | $383 | 4 Nov – 2 Dec · 28 nights | MDW → RSW | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
| Austin AUS | $392 | 21 Oct – 27 Oct · 6 nights | MDW → AUS | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
| Myrtle Beach MYR | $407 | 1 Dec – 3 Dec · 2 nights | MDW → MYR | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Oakland OAK | $484 | 8 Nov – 20 Nov · 12 nights | MDW → OAK | out nonstop, back 1 stop | found 6 days ago | See prices for these dates |
| Leon/Guanajuato BJX | $548 | 26 Oct – 29 Oct · 3 nights | MDW → BJX | out 2 stops, back nonstop | found 6 days ago | See prices for these dates |
| Indianapolis IND | $592 | 26 Oct – 26 Oct | MDW → IND | out 1 stop, back 2 stops | found 5 days ago | See prices for these dates |
| Honolulu HNL | $645 | 17 Jan 2027 – 24 Jan 2027 · 7 nights | MDW → HNL | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| San Antonio SAT | $665 | 21 Oct – 26 Oct · 5 nights | MDW → SAT | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| San Jose SJO | $679 | 11 Dec – 18 Dec · 7 nights | MDW → SJO | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Guayaquil GYE | $698 | 28 Jan 2027 – 17 Feb 2027 · 20 nights | MDW → GYE | out 3 stops, back 3 stops | found 6 days ago | See prices for these dates |
| Nassau NAS | $703 | 1 Dec – 31 Dec · 30 nights | MDW → NAS | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Barranquilla BAQ | $709 | 14 Dec – 19 Dec · 5 nights | MDW → BAQ | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Santo Domingo SDQ | $741 | 3 Nov – 8 Nov · 5 nights | MDW → SDQ | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Kahului OGG | $813 | 21 Feb 2027 – 6 Mar 2027 · 13 nights | MDW → OGG | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Lima LIM | $851 | 24 Nov – 1 Dec · 7 nights | MDW → LIM | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Reykjavik REK | $856 | 31 Dec – 23 Jan 2027 · 23 nights | MDW → KEF | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| Paris PAR | $912 | 30 Nov – 9 Dec · 9 nights | MDW → CDG | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
| Manila MNL | $918 | 11 Feb 2027 – 11 Mar 2027 · 28 nights | MDW → MNL | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| Medellin MDE | $972 | 5 Jan 2027 – 12 Jan 2027 · 7 nights | MDW → MDE | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| San Pedro Sula SAP | $1,023 | 1 Nov – 30 Nov · 29 nights | MDW → SAP | out 3 stops, back 2 stops | found 6 days ago | See prices for these dates |
| London LON | $1,026 | 1 Dec – 8 Dec · 7 nights | MDW → LHR | out 3 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Doha DOH | $1,095 | 3 Nov – 10 Nov · 7 nights | MDW → DOH | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Seoul SEL | $1,217 | 30 Nov – 6 Dec · 6 nights | MDW → ICN | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| Tokyo TYO | $1,222 | 24 Oct – 14 Nov · 21 nights | MDW → NRT | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Denpasar (Bali) DPS | $1,384 | 26 Oct – 1 Nov · 6 nights | MDW → DPS | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |
| Shenyang SHE | $1,407 | 26 Nov – 17 Dec · 21 nights | MDW → SHE | out 3 stops, back 3 stops | found 4 days ago | See prices for these dates |
| Papeete PPT | $1,504 | 25 Nov – 2 Dec · 7 nights | MDW → PPT | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Dubai DXB | $1,515 | 14 Mar 2027 – 20 Mar 2027 · 6 nights | MDW → DXB | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Suva SUV | $1,518 | 1 Dec – 5 Dec · 4 nights | MDW → SUV | out 2 stops, back 2 stops | found 5 days ago | See prices for these dates |
| Istanbul IST | $1,677 | 11 Jan 2027 – 17 Jan 2027 · 6 nights | MDW → IST | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| Fortaleza FOR | $1,709 | 19 Dec – 16 Jan 2027 · 28 nights | MDW → FOR | out 3 stops, back 3 stops | found 6 days ago | See prices for these dates |
| Samarkand SKD | $2,152 | 1 Nov – 16 Nov · 15 nights | MDW → SKD | out 2 stops, back 3 stops | found 6 days ago | See prices for these dates |
| Taipei TPE | $2,566 | 20 Dec – 1 Jan 2027 · 12 nights | MDW → TPE | out 3 stops, back 3 stops | found 5 days ago | See prices for these dates |
| Dushanbe DYU | $2,619 | 27 Oct – 28 Nov · 32 nights | MDW → DYU | out 2 stops, back 4 stops | found 6 days ago | See prices for these dates |
| Almaty ALA | $3,511 | 11 Dec – 9 Jan 2027 · 29 nights | MDW → ALA | out 2 stops, back 2 stops | found 6 days ago | See prices for these dates |